IL284068B - A process for producing fat-free oils and meal using solid/liquid extraction - Google Patents
A process for producing fat-free oils and meal using solid/liquid extractionInfo
- Publication number
- IL284068B IL284068B IL284068A IL28406821A IL284068B IL 284068 B IL284068 B IL 284068B IL 284068 A IL284068 A IL 284068A IL 28406821 A IL28406821 A IL 28406821A IL 284068 B IL284068 B IL 284068B
- Authority
- IL
- Israel
- Prior art keywords
- ppm
- weight
- methyloxolane
- solvent
- concentration
- Prior art date
Links
- 239000007787 solid Substances 0.000 title claims description 155
- 239000003921 oil Substances 0.000 title claims description 128
- 238000000034 method Methods 0.000 title claims description 120
- 238000000605 extraction Methods 0.000 title claims description 112
- 230000008569 process Effects 0.000 title claims description 103
- 239000007788 liquid Substances 0.000 title claims description 61
- 235000012054 meals Nutrition 0.000 title description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 146
- 239000002904 solvent Substances 0.000 claims description 146
- 239000010779 crude oil Substances 0.000 claims description 100
- 239000000758 substrate Substances 0.000 claims description 98
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 96
- 229910001868 water Inorganic materials 0.000 claims description 91
- 150000008442 polyphenolic compounds Chemical class 0.000 claims description 72
- 235000013824 polyphenols Nutrition 0.000 claims description 71
- 239000000203 mixture Substances 0.000 claims description 57
- 102000004169 proteins and genes Human genes 0.000 claims description 47
- 108090000623 proteins and genes Proteins 0.000 claims description 47
- 229930003799 tocopherol Natural products 0.000 claims description 44
- 239000011732 tocopherol Substances 0.000 claims description 44
- 239000006227 byproduct Substances 0.000 claims description 38
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 31
- 229960001295 tocopherol Drugs 0.000 claims description 31
- 235000010384 tocopherol Nutrition 0.000 claims description 31
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims description 31
- 235000010469 Glycine max Nutrition 0.000 claims description 28
- 244000068988 Glycine max Species 0.000 claims description 28
- 235000006008 Brassica napus var napus Nutrition 0.000 claims description 23
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims description 17
- 238000007670 refining Methods 0.000 claims description 16
- 238000004807 desolvation Methods 0.000 claims description 15
- 239000012141 concentrate Substances 0.000 claims description 13
- 235000013312 flour Nutrition 0.000 claims description 13
- 241000196324 Embryophyta Species 0.000 claims description 11
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 claims description 9
- 229920000742 Cotton Polymers 0.000 claims description 9
- 235000003222 Helianthus annuus Nutrition 0.000 claims description 9
- 240000008042 Zea mays Species 0.000 claims description 8
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 8
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 8
- 235000009973 maize Nutrition 0.000 claims description 8
- 235000003320 Adansonia digitata Nutrition 0.000 claims description 6
- 244000056971 Adansonia gregorii Species 0.000 claims description 6
- 235000003319 Adansonia gregorii Nutrition 0.000 claims description 6
- 244000060011 Cocos nucifera Species 0.000 claims description 6
- 235000013162 Cocos nucifera Nutrition 0.000 claims description 6
- 235000017060 Arachis glabrata Nutrition 0.000 claims description 5
- 244000105624 Arachis hypogaea Species 0.000 claims description 5
- 235000010777 Arachis hypogaea Nutrition 0.000 claims description 5
- 235000018262 Arachis monticola Nutrition 0.000 claims description 5
- 235000008753 Papaver somniferum Nutrition 0.000 claims description 5
- 235000020232 peanut Nutrition 0.000 claims description 5
- 238000011084 recovery Methods 0.000 claims description 5
- 235000000832 Ayote Nutrition 0.000 claims description 4
- 240000004244 Cucurbita moschata Species 0.000 claims description 4
- 235000009854 Cucurbita moschata Nutrition 0.000 claims description 4
- 235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 claims description 4
- 240000007049 Juglans regia Species 0.000 claims description 4
- 235000009496 Juglans regia Nutrition 0.000 claims description 4
- 240000001090 Papaver somniferum Species 0.000 claims description 4
- 240000001890 Ribes hudsonianum Species 0.000 claims description 4
- 235000016954 Ribes hudsonianum Nutrition 0.000 claims description 4
- 235000001466 Ribes nigrum Nutrition 0.000 claims description 4
- 235000015136 pumpkin Nutrition 0.000 claims description 4
- 235000020234 walnut Nutrition 0.000 claims description 4
- 244000144725 Amygdalus communis Species 0.000 claims description 3
- 235000011437 Amygdalus communis Nutrition 0.000 claims description 3
- 244000144730 Amygdalus persica Species 0.000 claims description 3
- 244000226021 Anacardium occidentale Species 0.000 claims description 3
- 240000005343 Azadirachta indica Species 0.000 claims description 3
- 244000017106 Bixa orellana Species 0.000 claims description 3
- 240000002791 Brassica napus Species 0.000 claims description 3
- 235000009590 Calophyllum inophyllum Nutrition 0.000 claims description 3
- 240000005589 Calophyllum inophyllum Species 0.000 claims description 3
- 235000009025 Carya illinoensis Nutrition 0.000 claims description 3
- 244000068645 Carya illinoensis Species 0.000 claims description 3
- 235000016071 Cordyline australis Nutrition 0.000 claims description 3
- 244000241257 Cucumis melo Species 0.000 claims description 3
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 claims description 3
- 235000014755 Eruca sativa Nutrition 0.000 claims description 3
- 244000024675 Eruca sativa Species 0.000 claims description 3
- 235000004431 Linum usitatissimum Nutrition 0.000 claims description 3
- 240000006240 Linum usitatissimum Species 0.000 claims description 3
- 241000219745 Lupinus Species 0.000 claims description 3
- 235000007688 Lycopersicon esculentum Nutrition 0.000 claims description 3
- 241001427678 Madhuca Species 0.000 claims description 3
- 235000013500 Melia azadirachta Nutrition 0.000 claims description 3
- 235000016698 Nigella sativa Nutrition 0.000 claims description 3
- 244000090896 Nigella sativa Species 0.000 claims description 3
- 235000014643 Orbignya martiana Nutrition 0.000 claims description 3
- 244000021150 Orbignya martiana Species 0.000 claims description 3
- 240000007594 Oryza sativa Species 0.000 claims description 3
- 235000007164 Oryza sativa Nutrition 0.000 claims description 3
- 235000004347 Perilla Nutrition 0.000 claims description 3
- 244000124853 Perilla frutescens Species 0.000 claims description 3
- 241001300674 Plukenetia volubilis Species 0.000 claims description 3
- 235000009827 Prunus armeniaca Nutrition 0.000 claims description 3
- 244000018633 Prunus armeniaca Species 0.000 claims description 3
- 235000006040 Prunus persica var persica Nutrition 0.000 claims description 3
- 240000004604 Ptychosperma elegans Species 0.000 claims description 3
- 244000294611 Punica granatum Species 0.000 claims description 3
- 235000014360 Punica granatum Nutrition 0.000 claims description 3
- 235000008947 Roystonea oleracea Nutrition 0.000 claims description 3
- 240000007651 Rubus glaucus Species 0.000 claims description 3
- 235000011034 Rubus glaucus Nutrition 0.000 claims description 3
- 235000009122 Rubus idaeus Nutrition 0.000 claims description 3
- 235000001601 Sabal palmetto Nutrition 0.000 claims description 3
- 235000003434 Sesamum indicum Nutrition 0.000 claims description 3
- 244000040738 Sesamum orientale Species 0.000 claims description 3
- 240000003768 Solanum lycopersicum Species 0.000 claims description 3
- 240000001717 Vaccinium macrocarpon Species 0.000 claims description 3
- 235000012545 Vaccinium macrocarpon Nutrition 0.000 claims description 3
- 235000002118 Vaccinium oxycoccus Nutrition 0.000 claims description 3
- 235000009754 Vitis X bourquina Nutrition 0.000 claims description 3
- 235000012333 Vitis X labruscana Nutrition 0.000 claims description 3
- 240000006365 Vitis vinifera Species 0.000 claims description 3
- 235000014787 Vitis vinifera Nutrition 0.000 claims description 3
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 claims description 3
- 235000020224 almond Nutrition 0.000 claims description 3
- 235000012665 annatto Nutrition 0.000 claims description 3
- 239000010362 annatto Substances 0.000 claims description 3
- 235000020226 cashew nut Nutrition 0.000 claims description 3
- 235000004634 cranberry Nutrition 0.000 claims description 3
- 244000005700 microbiome Species 0.000 claims description 3
- 239000001711 nigella sativa Substances 0.000 claims description 3
- 235000009566 rice Nutrition 0.000 claims description 3
- 230000001131 transforming effect Effects 0.000 claims description 3
- 235000009328 Amaranthus caudatus Nutrition 0.000 claims description 2
- 240000001592 Amaranthus caudatus Species 0.000 claims description 2
- 235000001274 Anacardium occidentale Nutrition 0.000 claims description 2
- 244000125300 Argania sideroxylon Species 0.000 claims description 2
- 235000002147 Australian walnut Nutrition 0.000 claims description 2
- 235000007319 Avena orientalis Nutrition 0.000 claims description 2
- 241000209763 Avena sativa Species 0.000 claims description 2
- 235000007558 Avena sp Nutrition 0.000 claims description 2
- 235000007689 Borago officinalis Nutrition 0.000 claims description 2
- 240000004355 Borago officinalis Species 0.000 claims description 2
- 235000003351 Brassica cretica Nutrition 0.000 claims description 2
- 235000003343 Brassica rupestris Nutrition 0.000 claims description 2
- 235000005881 Calendula officinalis Nutrition 0.000 claims description 2
- 235000016401 Camelina Nutrition 0.000 claims description 2
- 244000197813 Camelina sativa Species 0.000 claims description 2
- 244000025254 Cannabis sativa Species 0.000 claims description 2
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 claims description 2
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 claims description 2
- 235000002566 Capsicum Nutrition 0.000 claims description 2
- 240000004160 Capsicum annuum Species 0.000 claims description 2
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 claims description 2
- 235000003255 Carthamus tinctorius Nutrition 0.000 claims description 2
- 244000020518 Carthamus tinctorius Species 0.000 claims description 2
- 235000001543 Corylus americana Nutrition 0.000 claims description 2
- 240000007582 Corylus avellana Species 0.000 claims description 2
- 235000007466 Corylus avellana Nutrition 0.000 claims description 2
- 244000168525 Croton tiglium Species 0.000 claims description 2
- 235000002767 Daucus carota Nutrition 0.000 claims description 2
- 244000000626 Daucus carota Species 0.000 claims description 2
- 241001009357 Endiandra palmerstonii Species 0.000 claims description 2
- 240000000950 Hippophae rhamnoides Species 0.000 claims description 2
- 235000003145 Hippophae rhamnoides Nutrition 0.000 claims description 2
- 241000218228 Humulus Species 0.000 claims description 2
- 241000219925 Oenothera Species 0.000 claims description 2
- 235000004496 Oenothera biennis Nutrition 0.000 claims description 2
- 240000007817 Olea europaea Species 0.000 claims description 2
- 240000001439 Opuntia Species 0.000 claims description 2
- 235000013389 Opuntia humifusa var. humifusa Nutrition 0.000 claims description 2
- 239000006002 Pepper Substances 0.000 claims description 2
- 235000008673 Persea americana Nutrition 0.000 claims description 2
- 244000025272 Persea americana Species 0.000 claims description 2
- 235000016761 Piper aduncum Nutrition 0.000 claims description 2
- 240000003889 Piper guineense Species 0.000 claims description 2
- 235000017804 Piper guineense Nutrition 0.000 claims description 2
- 235000008184 Piper nigrum Nutrition 0.000 claims description 2
- 235000003447 Pistacia vera Nutrition 0.000 claims description 2
- 240000006711 Pistacia vera Species 0.000 claims description 2
- 240000000528 Ricinus communis Species 0.000 claims description 2
- 235000004443 Ricinus communis Nutrition 0.000 claims description 2
- 235000000657 Rosa moschata Nutrition 0.000 claims description 2
- 244000018676 Rosa sp Species 0.000 claims description 2
- 235000012377 Salvia columbariae var. columbariae Nutrition 0.000 claims description 2
- 240000005481 Salvia hispanica Species 0.000 claims description 2
- 235000001498 Salvia hispanica Nutrition 0.000 claims description 2
- 244000044822 Simmondsia californica Species 0.000 claims description 2
- 235000004433 Simmondsia californica Nutrition 0.000 claims description 2
- 240000000785 Tagetes erecta Species 0.000 claims description 2
- 235000009470 Theobroma cacao Nutrition 0.000 claims description 2
- 244000299461 Theobroma cacao Species 0.000 claims description 2
- 235000021307 Triticum Nutrition 0.000 claims description 2
- 244000098338 Triticum aestivum Species 0.000 claims description 2
- 235000012735 amaranth Nutrition 0.000 claims description 2
- 239000004178 amaranth Substances 0.000 claims description 2
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 claims description 2
- 235000009120 camo Nutrition 0.000 claims description 2
- 239000001511 capsicum annuum Substances 0.000 claims description 2
- 235000005607 chanvre indien Nutrition 0.000 claims description 2
- 235000014167 chia Nutrition 0.000 claims description 2
- 239000011487 hemp Substances 0.000 claims description 2
- 235000010460 mustard Nutrition 0.000 claims description 2
- 235000020233 pistachio Nutrition 0.000 claims description 2
- 244000056139 Brassica cretica Species 0.000 claims 1
- 244000020551 Helianthus annuus Species 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 137
- 235000019198 oils Nutrition 0.000 description 122
- 244000060924 Brassica campestris Species 0.000 description 20
- 230000000052 comparative effect Effects 0.000 description 19
- 238000004064 recycling Methods 0.000 description 17
- 238000004458 analytical method Methods 0.000 description 15
- 238000009833 condensation Methods 0.000 description 13
- 230000005494 condensation Effects 0.000 description 13
- 235000019149 tocopherols Nutrition 0.000 description 13
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 13
- 241001465754 Metazoa Species 0.000 description 12
- 235000013305 food Nutrition 0.000 description 12
- 239000000787 lecithin Substances 0.000 description 11
- 235000010445 lecithin Nutrition 0.000 description 11
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000009286 beneficial effect Effects 0.000 description 9
- 239000002537 cosmetic Substances 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- 241000208818 Helianthus Species 0.000 description 8
- 238000003306 harvesting Methods 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 235000016709 nutrition Nutrition 0.000 description 7
- 230000035764 nutrition Effects 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 235000020238 sunflower seed Nutrition 0.000 description 7
- 230000009466 transformation Effects 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 229940074391 gallic acid Drugs 0.000 description 5
- 235000004515 gallic acid Nutrition 0.000 description 5
- 238000000227 grinding Methods 0.000 description 5
- 230000036541 health Effects 0.000 description 5
- 238000002803 maceration Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000005070 sampling Methods 0.000 description 5
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 4
- 241000283690 Bos taurus Species 0.000 description 4
- 206010074268 Reproductive toxicity Diseases 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 230000029087 digestion Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 230000008821 health effect Effects 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 231100000189 neurotoxic Toxicity 0.000 description 4
- 230000002887 neurotoxic effect Effects 0.000 description 4
- 239000002417 nutraceutical Substances 0.000 description 4
- 235000021436 nutraceutical agent Nutrition 0.000 description 4
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 4
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 4
- 230000007696 reproductive toxicity Effects 0.000 description 4
- 231100000372 reproductive toxicity Toxicity 0.000 description 4
- 239000004575 stone Substances 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 3
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 3
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 3
- 208000024172 Cardiovascular disease Diseases 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000004061 bleaching Methods 0.000 description 3
- 238000011088 calibration curve Methods 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 238000013375 chromatographic separation Methods 0.000 description 3
- 238000005520 cutting process Methods 0.000 description 3
- 238000003795 desorption Methods 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 235000015872 dietary supplement Nutrition 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 235000021588 free fatty acids Nutrition 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 238000010297 mechanical methods and process Methods 0.000 description 3
- 230000005226 mechanical processes and functions Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000013557 residual solvent Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000000956 solid--liquid extraction Methods 0.000 description 3
- 238000001256 steam distillation Methods 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- 150000008163 sugars Chemical class 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 2
- 241000219146 Gossypium Species 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- 238000000944 Soxhlet extraction Methods 0.000 description 2
- 235000019728 animal nutrition Nutrition 0.000 description 2
- 235000019658 bitter taste Nutrition 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000009614 chemical analysis method Methods 0.000 description 2
- 229940060799 clarus Drugs 0.000 description 2
- 230000009089 cytolysis Effects 0.000 description 2
- 230000001877 deodorizing effect Effects 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000010200 folin Substances 0.000 description 2
- 230000037406 food intake Effects 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical compound O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 235000014571 nuts Nutrition 0.000 description 2
- 238000005325 percolation Methods 0.000 description 2
- 238000011020 pilot scale process Methods 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 230000003381 solubilizing effect Effects 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000035899 viability Effects 0.000 description 2
- 238000009369 viticulture Methods 0.000 description 2
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- DFGKGUXTPFWHIX-UHFFFAOYSA-N 6-[2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]acetyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)C1=CC2=C(NC(O2)=O)C=C1 DFGKGUXTPFWHIX-UHFFFAOYSA-N 0.000 description 1
- 241000609240 Ambelania acida Species 0.000 description 1
- 241001495180 Arthrospira Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 241000227752 Chaetoceros Species 0.000 description 1
- 241000195649 Chlorella <Chlorellales> Species 0.000 description 1
- 241000199913 Crypthecodinium Species 0.000 description 1
- 241001527609 Cryptococcus Species 0.000 description 1
- 241000195634 Dunaliella Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 235000003239 Guizotia abyssinica Nutrition 0.000 description 1
- 240000002795 Guizotia abyssinica Species 0.000 description 1
- 241000168525 Haematococcus Species 0.000 description 1
- 241001501885 Isochrysis Species 0.000 description 1
- 241000408747 Lepomis gibbosus Species 0.000 description 1
- 241001149698 Lipomyces Species 0.000 description 1
- 235000018330 Macadamia integrifolia Nutrition 0.000 description 1
- 235000003800 Macadamia tetraphylla Nutrition 0.000 description 1
- 240000000912 Macadamia tetraphylla Species 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 241000196305 Nannochloris Species 0.000 description 1
- 241000224474 Nannochloropsis Species 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 241000206731 Phaeodactylum Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000223252 Rhodotorula Species 0.000 description 1
- 241000235070 Saccharomyces Species 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 241000233671 Schizochytrium Species 0.000 description 1
- 238000010793 Steam injection (oil industry) Methods 0.000 description 1
- 241000223230 Trichosporon Species 0.000 description 1
- 241000235013 Yarrowia Species 0.000 description 1
- 238000011481 absorbance measurement Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 230000000433 anti-nutritional effect Effects 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000010905 bagasse Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 201000011529 cardiovascular cancer Diseases 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 1
- 235000020235 chia seed Nutrition 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- -1 gums Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000011806 microball Substances 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000019508 mustard seed Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229940038580 oat bran Drugs 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000001253 polyvinylpolypyrrolidone Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 235000005974 protein supplement Nutrition 0.000 description 1
- 229940116540 protein supplement Drugs 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 235000020236 pumpkin seed Nutrition 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
- A23D9/013—Other fatty acid esters, e.g. phosphatides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/02—Solvent extraction of solids
- B01D11/0288—Applications, solvents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/02—Solvent extraction of solids
- B01D11/0292—Treatment of the solvent
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B1/00—Production of fats or fatty oils from raw materials
- C11B1/10—Production of fats or fatty oils from raw materials by extracting
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/12—Refining fats or fatty oils by distillation
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/12—Refining fats or fatty oils by distillation
- C11B3/14—Refining fats or fatty oils by distillation with the use of indifferent gases or vapours, e.g. steam
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Microbiology (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Extraction Or Liquid Replacement (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Cosmetics (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1873103A FR3090008B1 (fr) | 2018-12-17 | 2018-12-17 | Procédé de production d'une huile brute riche en polyphénol par extraction solide/liquide |
PCT/FR2019/053125 WO2020128307A1 (fr) | 2018-12-17 | 2019-12-17 | Procédé de production d'huiles et de tourteaux dégraissés par extraction solide/liquide |
Publications (2)
Publication Number | Publication Date |
---|---|
IL284068A IL284068A (en) | 2021-08-31 |
IL284068B true IL284068B (en) | 2022-09-01 |
Family
ID=66676677
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IL284068A IL284068B (en) | 2018-12-17 | 2019-12-17 | A process for producing fat-free oils and meal using solid/liquid extraction |
Country Status (18)
Country | Link |
---|---|
US (1) | US11332691B2 (zh) |
EP (1) | EP3737736A1 (zh) |
JP (1) | JP7285921B2 (zh) |
KR (1) | KR102585796B1 (zh) |
CN (1) | CN111936607B (zh) |
AR (1) | AR117337A1 (zh) |
AU (2) | AU2019408740B2 (zh) |
BR (1) | BR112021009772A2 (zh) |
CA (2) | CA3171730A1 (zh) |
EA (1) | EA202191701A1 (zh) |
FR (1) | FR3090008B1 (zh) |
IL (1) | IL284068B (zh) |
MA (1) | MA51575A (zh) |
MX (1) | MX2021007234A (zh) |
UA (1) | UA128432C2 (zh) |
UY (1) | UY38508A (zh) |
WO (1) | WO2020128307A1 (zh) |
ZA (1) | ZA202104104B (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115372519A (zh) * | 2022-09-21 | 2022-11-22 | 广西壮族自治区水牛研究所 | 一种青贮饲料中乙醇的气相色谱检测方法 |
FR3140519A1 (fr) * | 2022-10-06 | 2024-04-12 | Pennakem Europa | Utilisation du 2-methyloxolane pour l'alimentation des animaux ovipares |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1144945B (it) | 1981-11-19 | 1986-10-29 | Anic Spa | Estrazione contemporanea di lipidi e polifenoli da mandorle laminate di girasole |
US6737088B1 (en) * | 1996-09-06 | 2004-05-18 | Mars, Incorporated | Cocoa extracts prepared from cocoa solids having high cocoa polyphenol contents |
CN1558942A (zh) * | 2001-09-28 | 2004-12-29 | 日清奥利友株式会社 | 含有齐墩果酸和/或山楂酸的油脂组合物的制造方法 |
GB2415136A (en) * | 2004-06-17 | 2005-12-21 | Natraceutical Sa | Obtaining olive polyphenol concentrate from a by-product of olive oil extraction using membrane separation techniques |
EP2163252A4 (en) * | 2007-05-17 | 2012-01-11 | Kaneka Corp | COMPOSITION CONTAINING A POLYPHENOL DERIVED FROM THE LICENSE |
FR2955782B1 (fr) * | 2010-01-29 | 2014-02-14 | Expanscience Lab | Extraction solide / liquide |
WO2012171987A1 (en) * | 2011-06-16 | 2012-12-20 | Lonza Ltd | A process for extraction of peptides and its application in liquid phase peptide synthesis |
-
2018
- 2018-12-17 FR FR1873103A patent/FR3090008B1/fr active Active
-
2019
- 2019-12-16 UY UY0001038508A patent/UY38508A/es unknown
- 2019-12-16 AR ARP190103684A patent/AR117337A1/es unknown
- 2019-12-16 CA CA3171730A patent/CA3171730A1/fr active Pending
- 2019-12-16 CA CA3065480A patent/CA3065480C/fr active Active
- 2019-12-17 AU AU2019408740A patent/AU2019408740B2/en active Active
- 2019-12-17 IL IL284068A patent/IL284068B/en unknown
- 2019-12-17 MA MA051575A patent/MA51575A/fr unknown
- 2019-12-17 CN CN201980022699.2A patent/CN111936607B/zh active Active
- 2019-12-17 EA EA202191701A patent/EA202191701A1/ru unknown
- 2019-12-17 UA UAA202103466A patent/UA128432C2/uk unknown
- 2019-12-17 BR BR112021009772-4A patent/BR112021009772A2/pt unknown
- 2019-12-17 KR KR1020217017134A patent/KR102585796B1/ko active IP Right Grant
- 2019-12-17 US US17/044,761 patent/US11332691B2/en active Active
- 2019-12-17 WO PCT/FR2019/053125 patent/WO2020128307A1/fr unknown
- 2019-12-17 JP JP2021518189A patent/JP7285921B2/ja active Active
- 2019-12-17 EP EP19842832.8A patent/EP3737736A1/fr active Pending
- 2019-12-17 MX MX2021007234A patent/MX2021007234A/es unknown
-
2021
- 2021-06-15 ZA ZA2021/04104A patent/ZA202104104B/en unknown
-
2022
- 2022-02-15 AU AU2022201003A patent/AU2022201003B2/en active Active
Also Published As
Publication number | Publication date |
---|---|
CA3065480A1 (fr) | 2020-06-17 |
EP3737736A1 (fr) | 2020-11-18 |
EA202191701A1 (ru) | 2021-09-03 |
CA3065480C (fr) | 2022-11-29 |
CN111936607A (zh) | 2020-11-13 |
ZA202104104B (en) | 2022-10-26 |
WO2020128307A1 (fr) | 2020-06-25 |
FR3090008A1 (fr) | 2020-06-19 |
US11332691B2 (en) | 2022-05-17 |
KR20210104687A (ko) | 2021-08-25 |
CA3171730A1 (fr) | 2020-06-17 |
MX2021007234A (es) | 2021-09-23 |
US20210108150A1 (en) | 2021-04-15 |
BR112021009772A2 (pt) | 2021-08-17 |
UY38508A (es) | 2020-07-31 |
AU2019408740A1 (en) | 2020-09-03 |
JP2022512273A (ja) | 2022-02-03 |
AR117337A1 (es) | 2021-07-28 |
AU2022201003B2 (en) | 2024-06-20 |
FR3090008B1 (fr) | 2023-03-31 |
AU2022201003A1 (en) | 2022-03-03 |
UA128432C2 (uk) | 2024-07-10 |
MA51575A (fr) | 2020-11-18 |
AU2019408740B2 (en) | 2021-12-23 |
CN111936607B (zh) | 2024-03-26 |
JP7285921B2 (ja) | 2023-06-02 |
IL284068A (en) | 2021-08-31 |
KR102585796B1 (ko) | 2023-10-10 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Chen et al. | Combining integrated ultrasonic-microwave technique with ethanol to maximise extraction of green coffee oil from Arabica coffee beans | |
Russin et al. | Alternative techniques for defatting soy: A practical review | |
WO2018000094A1 (en) | Decarboxylated cannabis resins, uses thereof and methods of making same | |
IL284068B (en) | A process for producing fat-free oils and meal using solid/liquid extraction | |
Wen et al. | Edible vegetable oils from oil crops: Preparation, refining, authenticity identification and application | |
Gadalkar et al. | Recovery of proteins from rice mill industry waste (rice bran) using alkaline or NaCl‐assisted alkaline extraction processes | |
US20230148638A1 (en) | Pongamia oil compositions, and methods for producing and using thereof | |
Jokić et al. | High-voltage electric discharge extraction of bioactive compounds from the cocoa bean shell | |
Song et al. | Ethanol‐assisted aqueous enzymatic extraction of peony seed oil | |
Lv et al. | Development of a new aqueous procedure for efficiently extracting high quality Camellia oleifera oil | |
Guo et al. | Extraction of rapeseed cake oil using subcritical R134a/butane: Process optimization and quality evaluation | |
Özcan et al. | Comparative of physico-chemical properties of wheat germ oil extracted with cold press and supercritical co2 extraction | |
WO2019207554A1 (en) | Extraction of compounds from cannabis biomass using food-grade solvent | |
Carré | About solvents used in the preparation of oils for cosmetic products complying with the Cosmos standard | |
Hung et al. | Optimal selectivity of ã-oryzanol and total phenolic compounds from rice bran using supercritical carbon dioxide fractionation technique | |
CN108285827B (zh) | 一种葡萄籽油及其制备方法 | |
CN102492543A (zh) | 一种辣椒籽油的生产工艺 | |
EA042984B1 (ru) | Способ получения растительного масла и обезжиренного жмыха экстракцией в системе твёрдое вещество-жидкость | |
Bodger et al. | An investivation of the extraction, refining and composition of oil from winged bean (Psophocarpus tetragonolobus [L.] DC) | |
Dunford et al. | Supercritical carbon dioxide fractionation of crude rice bran oil using a packed column with characterization of the resultant fractions | |
EP4454484A1 (en) | Water-soluble konjac corm extract and method for producing same | |
Krishna et al. | Use of Low Temperature for the Production of Superior Quality Rice Bran Oil | |
Chen et al. | Multi-frequency ultrasonic-assisted enzymatic extraction of coconut paring oil from coconut by-products: Impact on the yield, physicochemical properties, and emulsion stability | |
Adesina et al. | Investigating the impact of solvent extraction parameters on oil yield and oil properties: a review | |
Rewald | The phosphatides and oil in unroasted and roasted coffee beans |